Many formulations such as inks, paints, millbases and plastics materials require effective dispersants for uniformly distributing a particulate solid in an aqueous, a polar or a non-polar organic medium. For inks, it is desirable for ink manufacturers to generate printed products of high resolution and quality. The adaptability of printing process to cater for the ever widening range of base substrates, resins and pigments is a challenge. The pigment dispersion should be compatible with the different formulations used to ensure good adhesion and resistance of the final coating. Poor pigment dispersion or stabilisation can result in agglomeration or settling within the organic or aqueous liquid medium (e.g., ink, paint or coating) lowering the gloss and aesthetic appeal.
U.S. Pat. No. 7,265,197 (Huber et al., published 4 Sep. 2007) discloses dispersing pigments in ink compositions with a dispersant having formula:
where R1 is individually chosen from H and CH3, and n is an integer from 4 to 400).
International publication WO 2008/028954 (Thetford, published 13 Mar. 2008) discloses imide dispersant compounds containing terminal acidic groups in both a polar and a non-polar organic medium, where the dispersant compound is represented by the structure
where T is —(CH2)3— or —CH2CH(CH3)—; R′ is H or C1-50-optionally substituted hydrocarbyl group, or C1-50-optionally substituted hydrocarbonyl; Y is C2-4-alkyleneoxy; x is 2 to 90; and q is 1 or 2, with the proviso that in Formula (1a), when q is 1, T is —(CH2)3—, and when q is 2, T is —(CH2)3— or —CH2CH(CH3)—.
U.S. Pat. No. 5,688,312 (Sacripante et al., published 18 Nov. 1997) discloses an ink composition comprised of a colourant and an imide or bisimide. The imide or bisimide may be prepared by reacting phthalic anhydride and a mono- or di-amine.
International Patent Application WO 2007/139980 (Romanova et al., published, 6 Dec. 2007) discloses a reaction product of at least one di-anhydride with at least two reactants which are different from each other, each of which reactants contains a primary or secondary amino, hydroxyl or thiol functional group, and at least one of which reactants is polymeric.
U.S. Pat. No. 6,440,207 (Schulz, published 27 Aug. 2002) discloses a process for preparing dispersible dry organic pigments for aqueous systems containing one or more aromatic polyalkylene oxide dispersants. The aromatic polyalkylene oxide dispersant may be prepared by reacting in an autoclave containing 250 g of deionized water 19.8 (0.100 mol) of 1,8-naphthalic anhydride and 105 (0.105 mol) of Jeffamine™ XTJ-506 (83 wt % ethylene oxide, 17 wt % propylene oxide).
International Patent application PCT/US13/038114, filed 25 Apr. 2013, entitled “Aromatic Dispersant Composition” (by Shooter, Thetford and Richards) discloses a polymer comprising a polymer chain having at least one aromatic imide pendant group.
International Patent application PCT/US13/037928, filed 24 Apr. 2013, entitled “Aromatic Dispersant Composition” (by Shooter, Thetford and Richards) discloses a polymer comprising a polymer chain having at least one fused aromatic imide pendant group.
U.S. Pat. No. 5,128,393 (Peng et al., published 7 Jul. 1992) discloses a pigment dispersant that is the reaction product of an organic monoepoxide or polyepoxide with a primary amine containing an imidazoline moiety.
U.S. Pat. No. 5,324,756 (Gebregiorgis, published 28 Jun. 1994) discloses a pigment dispersant that has an advantage of allowing for the high pigment to binder ratios and minimizes the volatile organic content (VOC) in an electrocoating composition.
U.S. Pat. No. 8,236,157 (Gebregiorgis, published 21 Oct. 2010) discloses a pigment dispersing resin consists essentially of the carboxylic acid salt of an aminated bisphenol epoxy resin and an alkoxylated styrenated phenol.
U.S. Pat. No. 7,312,260 (Krappe et al., published 27 Jan. 2005) discloses addition compounds suitable for use as wetting agents and dispersants and obtainable by reacting monofunctional or polyfunctional aromatic epoxides with polyoxyalkylenemonoamines.
US Patent Application 2006/0089426 (Haubennestel et al., published 27 Apr. 2006) discloses alkoxylated epoxide-amine adducts having a number-average molecular weight of more than 500 g/mol.
US Patent Application 2009/0221745 (Orth et al., published 3 Sep. 2009) discloses a compound suitable as a wetting and dispersing agent and obtainable from the reaction of A) polyepoxides with B) at least one aliphatic and/or araliphatic primary amine, and C) a modified polyalkoxylate isocyanate to form a urethane.
US Patent Application 2008/0047462 (Klein et al., published 28 Feb. 2008) discloses a composition of matter useful as an ink, which composition comprises a solvent, a pigment, and an effective pigment-dispersing amount of a water-soluble dispersant of a given structure.
US Patent Application 2008/0119613 (Klein et al, published 22 May 2008) discloses water-soluble products formed by reacting a monofunctional, amine-terminated polyether with a glycidyl ether of a polyol.
US Patent Application 2010/0227950 (Nguyen et al., published 9 Sep. 2010) discloses a pigment component, an effective pigment-dispersing amount of a dispersant of the given formula.
U.S. Pat. No. 5,852,123 (Huybrechts, published 22 Dec. 1998) discloses polymeric dispersant for pigments based on an acrylic graft copolymer wherein the graft copolymer has at least about 1 weight percent of an imide or urea functional dispersing substituent attached to the backbone, the macromonomer, or both the backbone and the macromonomer.
International publication WO 00/12582 A (Simms et al., published 9 Mar. 2000) discloses a polymeric pigment dispersant of a graft polymer having an acrylic polymer backbone and pending from the backbone, polyester side chains, cyclic imide groups and quaternary ammonium groups.
Japanese patent application JP2013-053200A (Tanaka et al., published 2 Sep. 2011) discloses dispersions comprising cyclic imide-containing aqueous polyurethanes as dispersing resins, pigments, and dispersants.
U.S. Pat. No. 5,424,346 (Simms et al., published 13 Jun. 1995) discloses polyester/acrylic comb polymers which are the reaction product of 20-85% of a carboxylic functional polyester copolymer, 10-50% of an oxirane substituted acrylic copolymer, and 2 to 20% of an imide compound having an isoindolino group.
Japanese Patent Application JP2012-211228 A (Murakami et al., published 1 Nov. 2012) discloses a A-B block copolymer having MW 500-5,000. The polymer block A constitutes methacrylic acid a constituent at least, and polymer block of B has two or more carboxyl groups,
Journal article entitled “A new graft copolymer pigment dispersant synthesis” published in Progress in Organic Coatings 35 (1999) 205-214 discloses grafting phthalimide onto an epoxide functional acrylate.